Dialkyl 3-dodecyloxypropane-1-phosphonate



Patented Dec. 29, 1953 UNITED STATES DIALKYL 3-DODECYLOXYPROPANE-1-PHOSPHQNATE Elbert C. Ladd and Merlin N. J., assignors to United P.Harvey, Passaic, States Rubber Company, New York, N. Y., a corporationof New Jersey No Drawing. Application November 3, 1950, Serial No.194,022

2 Claims.

This invention relates to the preparation of certain dialkyl propanephosphonates by the free-radical-catalyzed reaction of a dialkylphosphite and allyl dodecyl ether. The alkyl groups of the phosphite mayeach contain from 1 to 4 carbon atoms.

This application is a continuation-in-part of application Serial No.38,188, filed July 12, 1948, now abandoned.

The following example is illustrative of the manner of preparation.

Example 45.28 parts of allyl dodecyl ether are heated with 56 parts ofdiethyl phosphite at 80-85 C. for 38 hours during which time 1.2 partsof benzoyl peroxide are added in 4 equal increments at 0, 5.5, 14. and23 hours of elapsed reaction time. The reaction mixture is fractionallydistilled under reduced pressure, 41.9 parts of unreacted diethylphosphite and 23.9 parts of allyl dodecyl ether being recovered, then30.2 parts of high-boiling liquid residue (b. 192/0.9 mm.) consisting ofdiethyl 3-dodecycloxypropane-1-phosphonate.

Analysis-Calculated: C, 62.60; H, 11.34; P. 8.50. Found: C, 63.02; H,11.29; P. 7.59.

The chemicals may be used as plasticizers for polyvinyl chloride.

The products have in the molecule thereof the components of one moleculeof the phosphite and one molecule of the ether.

The temperature and time of the reaction may vary widely depending onthe source of free radicals which may be ultra-violet light or acatalyst of the class of peroxidic com ounds (e. g., benzoyl peroxide,tert.-butyl hydroperoxide, acetyl peroxide, hydrogen peroxide, potassiumperoxysulfate), hydrazine and substituted hydrazines, azobenzene, andmetal alkyls (e. g., sodium ethyl and lead tetraethyl), the amount ofsuch eatalyst compound employed being usually in the range of from 0.1to 15.0% by weight of the reactant mixture.

The reaction temperatures are preferably C. to C. (when using benzoylperoxide), and the time preferably 2 to 48 hours.

Having thus described our invention, what we claim and desire to protectby Letters Patent is:

1. A dialkyl 3-dodecyloxypropane-l-phosphonate.

2. Diethyl 3 dodecyloxypropane-l-phosphonate.

ELBERT C. LADD. MERLIN P. HARVEY.

References Cited in the file of this patent UNITED STATES PATENTS NumberName Date 2,440,800 Hanford II May 4, 1948 2,478,390 Hanford et al Aug.9, 1949 2,492,994 Harman et a1 Jan. 3, 1950 2.500.022 Brown Mar. '7. 1502,535,172 Tawney Dec. 26, 1950

1. A DIALKY 3-DODECYLOXYPROPANE-1-PHOSPHONATE.